Hydrogen Bromide → 2-Methyl-4-octylaminoquinolin-6-ol hydrobromide hemihydrate

HRID 1720268Notes

Reaction equation

HRID 1720268 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[BrH:15].[CH2:16]([NH2:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[OH2:12].[BrH:15].[CH3:14][C:4]1[CH:3]=[C:2]([NH:24][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=1.[CH3:14][C:4]1[CH:3]=[C:2]([NH:24][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=1.[BrH:15]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 8143OctylamineHCID 6101144-Chloro-6-methoxy-2-methylquinoline

Product 1

HCID 677650142-Methyl-4-octylaminoquinolin-6-ol hydrobromide hemihydrateYield 12%

Procedure

In a 100 mL three-neck round bottom flask under a nitrogen atmosphere and with magnetic stirring, a solution of 1.0 g (4.8 mmol) of 4-chloro-6-methoxy-2-methylquinoline and 10 mL of n-octylamine was heated under reflux for three hours. Upon cooling to room temperature, the reaction mixture formed a glassy solid which was filtered. This was triturated under isopropyl ether filtered and washed with additional ether. The solid was stirred with a mixture of water and ethyl acetate; insolubles were filtered and discarded; the ethyl acetate layer eventually furnished 500 mg of 6-methoxy-2-methyl-N-octylquinolin-4-amine hydrochloride: m.p. 178°-179° C. Without further purification, a solution of 350 mg (1.04 mmol) of this material and 42 mL of 48% hydrobromic acid was heated reflux for 18 hours. Upon cooling, the reaction solution gave a precipitate which was filtered. The filtrate was evaporated to furnish a solid residue. The combined solids were recrystallized from hot water to give 45 mg (12%) of 2-methyl-4-octylaminoquinolin-6-ol hydrobromide hemihydrate: m.p. 176°-178° C.

Workup

  1. temperatureunder reflux for three hours
  2. customthe reaction mixture formed a glassy solid which
  3. filtrationwas filtered
  4. customThis was triturated under isopropyl ether
  5. filtrationfiltered
  6. washwashed with additional ether
  7. filtrationinsolubles were filtered
  8. customWithout further purification
  9. temperaturereflux for 18 hours
  10. temperatureUpon cooling
  11. customthe reaction solution gave a precipitate which
  12. filtrationwas filtered
  13. customThe filtrate was evaporated
  14. customto furnish a solid residue
  15. customThe combined solids were recrystallized from hot water

Sources & evidence

ORD record
ord-e4541ae56af44ffcbb498076669299da
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

Loading…